4-iodo-5,5-dimethylfuran-2(5H)-one | 869885-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-iodo-5,5-dimethylfuran-2(5H)-one
• 英文别名: 4-Iodo-5,5-dimethylfuran-2-one
• CAS: 869885-30-3
• 化学式: C₆H₇IO₂
• 分子量: 238.025
• InChiKey: FMKBXHAEKDTBFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodo-5,5-dimethylfuran-2(5H)-one 、 (1-(allyloxy)prop-2-ynyl)benzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到3,3-dimethyl-5-phenyl-4,7,7a,8-tetrahydro-1H,3H-benzo[1,2-c:4,5-c']difuran-1-one
  参考文献：
  名称：

  Pd-Catalyzed Sequential Reactions via Allene Intermediate for the Synthesis of Polycyclic Frameworks Containing 2,3-Dihydrofuran Units

  摘要：

  A stepwise process involving Sonogashira coupling, propargyl allenyl isomerization, and consecutive [4 + 2] cyclization has been realized, leading to an efficient synthesis of polycyclic compounds containing a 2,3-dihydrofuran unit. Most attractive for synthetic interest is the finding that up to four stereogenic centers could be generated in one step with high stereoselectivity.

  DOI：

  10.1021/ol801139b
• 作为产物：
  描述：

  4-methyl-penta-2,3-dienoic acid ethyl ester 在 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以60%的产率得到4-iodo-5,5-dimethylfuran-2(5H)-one
  参考文献：
  名称：

  通过 2,3-烯丙酸酯与 I2 的碘内酯化反应有效制备 4-Iodofuran-2(5H)-ones

  摘要：

  通过羰基氧原子直接参与区域选择性亲电加成，在 MeCN 水溶液中，通过 2,3-烯丙酸乙酯与 I2 的轻松碘内酯化，以中等至高产率制备 4-Iodofuran-2(5H)-ones。丙二烯部分。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200500296

文献信息

• Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives
  作者：Xian Huang、Shugao Zhu、Ruwei Shen

  DOI：10.1002/adsc.200900503

  日期：2009.12

  In this paper, we report a novel sequential reaction sequence consisting of a series of processes including Sonogashira coupling, propargyl-allenyl isomerization, [3+2] cycloaddition, denitrogenation, and highly selective biradical coupling reaction, providing an efficient synthesis of fused polycyclic pyrrole derivatives. The reaction features one CC bond and two CN bonds formed to construct the pyrrole

  在本文中，我们报告了一种新颖的顺序反应序列，该序列由一系列过程组成，包括Sonogashira偶联，炔丙基-烯丙基异构化，[3 + 2]环加成，脱氮和高度选择性的双自由基偶联反应，可提供稠合多环吡咯的有效合成衍生品。该反应的特征是形成一个CC键和两个CN键以构建吡咯单元，以及在一个冲程中有效组装的两个环。
• Facile Synthesis of Polycyclic Fluorene Derivatives<i>via</i>a Palladium-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Schmittel Cyclization Sequence
  作者：Ruwei Shen、Linzhu Chen、Xian Huang

  DOI：10.1002/adsc.200900600

  日期：2009.11

  A stepwise process involving Sonogashira coupling, propargyl-allenyl isomerization and Schmittel cyclization has been realized, leading to an efficient synthesis of polycyclic fluorene derivatives from readily available starting materials. The reaction features the formation of three new carbon-carbon bonds to construct the benzene unit together with an efficient assembly of three or four rings in

  已经实现了涉及Sonogashira偶联，炔丙基-烯基异构化和Schmittel环化的逐步过程，从而导致了从容易获得的起始原料有效合成多环芴衍生物的方法。该反应的特征是在一个操作步骤中形成了三个新的碳-碳键以构建苯单元，以及三个或四个环的有效组装。
• Facile 5-endo electrophilic cyclization of unsaturated amides with tBuOCl/I2
  作者：Yu Tang、Chaozhong Li

  DOI：10.1016/j.tetlet.2006.03.166

  日期：2006.6

  5-Endo iodocyclization of various beta,gamma-unsaturated amides proceeded smoothly to give the corresponding conjugated imino-lactones exclusively in satisfactory yields with the use of (BuOCl)-Bu-1 and I-2 as the reagents, which proved to be much advantageous over the conventional I-2/NaHCO3. (c) 2006 Elsevier Ltd. All rights reserved.
• Efficient Preparation of 4-Iodofuran-2(5H)-ones by Iodolactonisation of 2,3-Allenoates with I2
  作者：Chunling Fu、Shengming Ma

  DOI：10.1002/ejoc.200500296

  日期：2005.9

  4-Iodofuran-2(5H)-ones were prepared, in moderate to high yields, by the facile iodolactonisation of ethyl 2,3-allenoates with I2 in aqueous MeCN by the direct participation of the carbonyl oxygen atom in the regioselective electrophilic addition of the allene moiety. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  通过羰基氧原子直接参与区域选择性亲电加成，在 MeCN 水溶液中，通过 2,3-烯丙酸乙酯与 I2 的轻松碘内酯化，以中等至高产率制备 4-Iodofuran-2(5H)-ones。丙二烯部分。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Pd-Catalyzed Sequential Reactions via Allene Intermediate for the Synthesis of Polycyclic Frameworks Containing 2,3-Dihydrofuran Units
  作者：Ruwei Shen、Xian Huang

  DOI：10.1021/ol801139b

  日期：2008.8.7

  A stepwise process involving Sonogashira coupling, propargyl allenyl isomerization, and consecutive [4 + 2] cyclization has been realized, leading to an efficient synthesis of polycyclic compounds containing a 2,3-dihydrofuran unit. Most attractive for synthetic interest is the finding that up to four stereogenic centers could be generated in one step with high stereoselectivity.